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YC Applicants: Q&A with Abby and Ivan Kirigin of Tipjoy
69 points by releasedatez on Feb 23, 2009 | hide | past | favorite | 10 comments
I have recently exchanged Q&A emails with Ivan Kirigin, the founder of tipjoy.com, about his experiences being in the Y Combinator. I want to really thank Ivan and Abby for replying all these questions with depth. I've promised I would share these Q&A with the community so all YC applicants can have a taste and feel of what's to come and more importantly what the application process is like.

I also want to thank Andrew Warner from mixergy.com for helping me and inspiring me to apply for Y Combinator. If you ever need to learn entrepreneurship, his interviews is a great way to learn it from.

Here's the Q&A:

Q: Did you have to assist the financial risks that were involved with both of you in the same business? Isn't it like putting all your eggs in one basket?

The worst case scenario was that we would have to go back to 'regular' jobs. Leaving a job at a big company to start your own company is probably the best reason to leave, and it is important to keep ties with that world so that you can rejoin it if need be. We figured out how much time we had before needing to move forward with this "nuclear option". We just keep aware of our runway so we don't get surprised. Between our savings and our investors, we've been able to be secure.

Q: What was your overall Y Combinator application experience like?

I told Abby about it in summer 2007, saying it might be for college students. She looked it over and thought it was good for any company. We'd been reading lots of Paul Graham's essays and thought YC's approach was exceptionally creative. We edited our application over time, crafting the message and wording a lot. Working through the application like this really helped us refine our idea, our goals, and our vision. It was very valuable. Once we were accepted to the interview, we practiced pitching to a few friends and colleagues. It was amazing how much our approach to talking about and presenting Tipjoy evolved during those sessions.

The interview was definitely not what we expected. We butted heads with Paul quite a bit. There were some user experience approaches which Abby felt were key to what we were doing. Although the UX approaches don't add up to the entire product, YC's main concern was that we were so passionate about our idea that we might not be willing to alter it if the market demanded. Abby thought we didn't get in. I wasn't sure. Ultimately they must have enjoyed the debate because we were accepted! Working with YC has been an amazing experience.

Q: Besides submitting an application, did you do anything extra to help you get into the interview round with Y Combinator?

We had a demo system live that I'm pretty sure they didn't look at. Making it was a good exercise for us though.

Q: What was your interview experience like? Do you have any advice for the new applicants this year?

Lots of people make the mistake of assuming the interview is a presentation. That's not the format. It's a conversation with maybe a 3-second demo component. They asked a lot of questions right away and that guided the conversation. I'd recommend practicing by pitching to people that understand your market.

Q: When you got funding by Y Combinator, did you have to give up a lot to move to California? How did you feel right before you moved?

We had to move from Arlington, Massachusetts. We had a house, which we kept and eventually moved back into after moving back to Massachusetts. We had a spot in a nursery school for our son, which we also managed to keep. Really we didn't have to 'give up' anything. Everything that mattered was coming with us.

Once we knew we were moving (of course we accepted YC's offer right away), Abby spent a lot of time getting all the logistics worked out. She found a temporary place for us to live in Mountain View which would work for our family. In addition to our son Luka, we brought our dog and also my mom who came to live with us and take care of our son Luka full-time. When it came time for the move, my brother helped me drive a carful of stuff across the country. We owe a lot to our family who are always there to help.

We were very excited to move. It felt a bit crazy like a fox, but the opportunity was too big to pass up.

In fact it was great that we were taken out of our normal routine and life in MA. That way we were able to completely focus on building Tipjoy. It was also great to spend several months entrenched in the Valley network.

Taking this leap together has been pretty amazing. Our company and our family are stronger and richer from the experience.



The demo probably was about 3 seconds. Look at tipjoy.com for 1.5 seconds, and you can tell what it's for and that it's cool and alive. In the other 1.5 seconds you can tip someone 25 cents for their blog entry. It's that easy and obvious.

Practice giving punchy demos. Don't frikkin make us watch you log in. We should be saying oooh at the 2 second mark, aaah at 5 seconds, and wow at 10 seconds. Definitely get all the best bits in the first 10 seconds.

10 seconds may sound flippant. But actual users will have clicked the back button long before if they aren't engaged.

You can practice demoing successful websites. Imagine you were pitching Google or eBay or Tokbox or justin.tv and had 10 seconds to demo. Start logged in. Assume some users won't see the last 5 seconds.


This is very good advice and the interview, as short as it was, is very inspiring.


Good stuff. Some more advice from the same folks:

http://tipjoys2cents.blogspot.com/2008/03/how-to-hack-togeth...

http://tipjoys2cents.blogspot.com/2008/03/yc-applications-ar...

From others:

http://leavingcorporate.com/2008/03/24/how-to-get-accepted-f...

http://mattmaroon.com/?p=247


some really good links thanks


thanks for these additional links. They were helpful.


YC alumni keep amazing me with how much help they're willing to give other entrepreneurs. releasedatez, great interview.


Me and my co-founder flew out last summer for YC interviews and weren't accepted. This is my advice.

We had been accepted for the interview and for a good two or three weeks we dropped just about everything. Stopped going to class, stopped going to work, and more or less just hacked on the demo. Even in the airport, on the plane and in the hotel we kept hacking. This demo was kicking ass. We also talked a bit about our talking points and plan for the interview.

On the day of, we walked into Y-Combinator, chatted with some of the other applicants about what we all were working on, played with a robot from Anybots that was wandering around, ate some snacks and then went into the interview room. As soon as we entered the room, we greeted everyone , and went to sit down. The plan was to have my co-founder start talking and I'd plug in the laptop and bring up the demo. Before either of us could do anything (literally as soon as the last hand shake was over) we started getting questions thrown at us. I mean thrown. This was kind of unexpected, as we thought it'd be more of us talking, presenting, and answering... but for a good solid 10 minutes we were sitting across from 3 people who never let up. As soon as we'd start answering 1 question, we'd get 2 others thrown at us when we were 3 words into our answer. This was at first misleading to me (as it seemed they didn't have time to listen to our answer)... but you quickly realize what questions are being asked and why and how satisfied they were with the previous answers. Generally the sooner they cut you off, the more pleased they seemed with what you said. You only have 10 minutes, so as soon as they hear what they want to, they tended to move along.

We did a quick demo, really quick... measured in seconds but closer to 60 than to 3. We spent weeks working on the demo, and it turned out to potentially be the least significant part of the whole interview. They liked knowing there was a demo, they like seeing it and getting a quick feel for our capabilities and general direction... but that took about 15 seconds for them to get a grasp on, not a 2 minute demo.

We left uncertain of the outcome, but glad we'd just gone through the intense session. We'd never pitched before, and it was good to know that we just walked out of the door having gotten some great experience pitching to the best.

Later that night we got an email from Paul that was really well written and insightful. The gist of the email was that they loved the team, the demo, and the idea but not how we intended to monetize it. We've since refocused on a more specific problem (in the same domain) that we feel we've solved more adequately than anyone in the field. We've also decided to continue bootstrapping for now. The lessons learned are:

1. You can have the greatest product in the world, but no one will care if you can't talk about it. We should have spent more time preparing for questions than hacking. We aced all of the phone screens, and we wrote everything from scratch so we felt we could easily answer any questions tossed at us. We should have spent more time fielding practice questions.

2. We should have discussed monetization more. We had a plan, but perhaps it was a little too optimistic. We refused to just say "ads", we wanted real users paying for this and our approach at the time could have used some refinement.

3. Enjoy the experience. We didn't get accepted, but still learned a great deal. Paul's email is still referenced to this day. The interview inspired us to revisit what we were doing. Looking back a year, I'm much happier with the product we have now. We went back to the drawing board and came out with a much stronger approach and idea.

4. Apply. Just filling out the application will make you more aware of your startup than you are right now. I guarantee it.

5. Don't give up just because you weren't accepted. If your idea is any good, you'll have to "ram it down their throats" anyway.

The only major downside is that we currently both have 9-to-5's and it really cuts into productivity. Bootstrapping is hard.

We came out of the process better than we were going into it. We probably won't be applying again this cycle because we're hoping to finally push live what we've been working on. We'll almost definitely pursue investors after the push though, we just don't need the distraction right now.


I was accepted for an interview and then funding last summer, but decided not to take it for various reasons. I wrote my advice to someone here on Hacker News, as you did, then expanded on it in a blog post:

http://www.jperla.com/blog/2008/07/20/ycombinator-applicatio...


Thank you for sharing such a detailed insight. This is very helpful because hearing it from a team that didn't get in can aid the applicants to look at aspects they might have missed.


Thanks to both releasedatez and Ivan Kirigin for taking the time to post this. Not an amazing amount of substance, but still some interesting bits with a few insight into yc's process.




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